Production Method 1

1073-06-9

811711-33-8

Reaction Conditions

Reference

Product class 3: bromoarenes

Stanforth, S. P., Science of Synthesis, 2007, 31, 121-160

Production Method 2

1073-06-9

811711-33-8

Reaction Conditions

1.1 Reagents: Butyllithium ,  2,2,6,6-Tetramethylpiperidine Solvents: Tetrahydrofuran ,  Hexane ;  30 min, -20 °C; -20 °C → -78 °C; 2 h, < -70 °C
1.2 Reagents: Zinc chloride Solvents: Tetrahydrofuran ;  30 min, < -70 °C
1.3 Reagents: Bromine ;  < 30 min, < -50 °C; -50 °C → rt
1.4 Reagents: Water ;  rt

Reference

An Improved Method for the Bromination of Metalated Haloarenes via Lithium, Zinc Transmetalation: A Convenient Synthesis of 1,2-Dibromoarenes

Menzel, Karsten; et al, Journal of Organic Chemistry, 2006, 71(5), 2188-2191

Production Method 3

1073-06-9

811711-33-8

Reaction Conditions

1.1 Reagents: Diisopropylamine ,  Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 2 h, -78 °C
1.2 Reagents: 1,2-Dibromo-1,1,2,2-tetrafluoroethane ;  -78 °C; 0.5 h, -78 °C; -78 °C → 25 °C
1.3 Reagents: Water ;  25 °C

Reference

Efficient and Complementary Methods Offering Access to Synthetically Valuable 1,2-Dibromobenzenes

Diemer, Vincent; et al, European Journal of Organic Chemistry, 2011, (2), 327-340

1,2-Dibromo-3-fluorobenzene Raw materials

• 1-Bromo-3-fluorobenzene

1,2-Dibromo-3-fluorobenzene Preparation Products

• 1,2-Dibromo-3-fluorobenzene (811711-33-8)

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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Halobenzenes Fluorobenzenes

Introduction to 1,2-Dibromo-3-fluorobenzene (CAS No. 811711-33-8)

1,2-Dibromo-3-fluorobenzene, with the chemical formula C?H?Br?F, is a halogenated aromatic compound that has garnered significant attention in the field of organic synthesis and pharmaceutical chemistry. This compound belongs to the class of brominated and fluorinated benzenes, which are widely utilized as intermediates in the synthesis of various active pharmaceutical ingredients (APIs) and specialty chemicals. The unique combination of bromine and fluorine substituents on the benzene ring imparts distinct reactivity and electronic properties, making it a valuable building block for further functionalization.

The CAS No. 811711-33-8 uniquely identifies this compound in scientific literature and commercial databases, ensuring precise referencing and compliance with regulatory standards. The structural features of 1,2-Dibromo-3-fluorobenzene include two bromine atoms at the 1 and 2 positions, and a fluorine atom at the 3 position, which create a highly reactive system for various chemical transformations. These substituents influence the electronic distribution across the ring, enhancing its utility in cross-coupling reactions, nucleophilic substitutions, and other synthetic methodologies.

In recent years, 1,2-Dibromo-3-fluorobenzene has been extensively studied for its role in medicinal chemistry. The presence of both bromine and fluorine atoms makes it an excellent precursor for the synthesis of more complex molecules. For instance, the bromine atoms can be selectively removed or replaced using palladium-catalyzed cross-coupling reactions, while the fluorine atom can serve as a handle for further derivatization. These properties have made it a preferred choice for researchers developing new therapeutic agents.

One of the most notable applications of 1,2-Dibromo-3-fluorobenzene is in the synthesis of antiviral and anticancer compounds. The halogenated aromatic core is a common motif in many drugs that target viral enzymes or inhibit tumor growth. Recent studies have demonstrated its utility in generating novel inhibitors of viral proteases and kinases. For example, derivatives of 1,2-Dibromo-3-fluorobenzene have been shown to exhibit potent activity against influenza virus by inhibiting the neuraminidase enzyme.

Moreover, the compound has been explored in the development of small-molecule probes for biochemical studies. The ability to introduce fluorine labels allows researchers to track metabolic pathways and protein interactions using advanced imaging techniques. Fluorinated compounds are particularly useful in magnetic resonance imaging (MRI) due to their high relaxivity and stability. Thus, 1,2-Dibromo-3-fluorobenzene serves as a versatile tool for both drug discovery and fundamental biological research.

The synthetic methodologies involving 1,2-Dibromo-3-fluorobenzene have also seen significant advancements. Modern catalytic systems have enabled more efficient and selective transformations, reducing waste and improving yields. For instance, transition metal-catalyzed C-H activation has opened new avenues for constructing complex molecular architectures from simple precursors like 1,2-Dibromo-3-fluorobenzene. These innovations are crucial for sustainable chemistry and have accelerated the discovery of novel bioactive compounds.

In conclusion, 1,2-Dibromo-3-fluorobenzene (CAS No. 811711-33-8) is a multifaceted compound with broad applications in pharmaceuticals and chemical research. Its unique structural features make it an indispensable intermediate for synthesizing a wide range of bioactive molecules. As research continues to uncover new therapeutic targets and synthetic strategies, the importance of this compound is expected to grow further. The ongoing development of innovative synthetic techniques will continue to enhance its utility in both academic and industrial settings.

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